Shelter Island Vacations from ₩1,007,504
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The Latest Shelter Island Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Shelburne Sonesta New York
Manhattan
Price was ₩1,358,706, price is now ₩1,007,504 per person
₩1,007,504
per person
May 29 - Jun 1
found 3 hours ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (2,031 reviews)
Stayed with our pup. Rooftop dining was perfection!
Reviewed on Apr 15, 2026
Hotel Riu Plaza New York Times Square
Manhattan
Save 100% on your flight
Price was ₩2,159,793, price is now ₩1,522,870 per person
₩1,522,870
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (2,951 reviews)
The staff was extremely helpful in answering any questions we had and providing recommendations for restaurants and directions. The rooms and property were always clean. Breakfast provided many choices da and was always well stocked. The breakfast bone moves quickly and efficiently. The frosted glass shower/bathroom wall” was NOT an issue as the person in the bathroom could only be seen as a “blob.”
Reviewed on Apr 14, 2026
Hotel St. James
Manhattan
Price was ₩1,426,274, price is now ₩1,014,069 per person
₩1,014,069
per person
May 29 - Jun 1
found 3 hours ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (7,108 reviews)
The staff was wonderful!!! The property was very clean and we felt very safe and comfortable. It is definitely a dated property. It isn’t fancy but it is very comfortable. The staff truly went above and beyond. The location is also very convenient.
Reviewed on Apr 15, 2026
Tempo by Hilton New York Times Square
Manhattan
Price was ₩1,616,326, price is now ₩1,206,029 per person
₩1,206,029
per person
May 29 - Jun 1
found 3 hours ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (5,525 reviews)
Great location, clean hotel, and friendly staff.
Reviewed on Apr 15, 2026
Chelsea Savoy Hotel
Manhattan
Price was ₩1,433,032, price is now ₩1,077,498 per person
₩1,077,498
per person
May 29 - Jun 1
found 3 hours ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
8.6/10 Excellent! (2,456 reviews)
Great budget location between financial district and Times Square. Easy subway access. Simple bagel and coffee breakfast. Street side rooms hear outside happenings. Staff was helpful and friendly. We would stay again.
Reviewed on Apr 15, 2026
Where to stay in Shelter Island
Find the best Shelter Island areas and neighborhoods for the activities you enjoy most. Learn more about Shelter Island
Silver Beach
While Silver Beach might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Sunset Beach and Crescent Beach.
Find the Best Shelter Island Vacation Packages
Shelter Island Beach Vacation
There's nothing like a Shelter Island vacation to give you a little extra bounce in your step. The sound of rolling surf and the smell of clean ocean air are sure to refresh your mind, body and soul. To be close to the town center on your trip to Shelter Island, find a hotel around Wades Beach (2 kilometers away). If you're planning to stay for a bit, look into our Shelter Island packages. Not only can you save some cash, you'll also have other amazing beaches near you to explore, like Shell Beach and Menhadden Lane Beach.
Shelter Island Hotel Deals
Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway Montauk NY
The price is ₩853,905 per night from Apr 29 to Apr 30
₩853,905
₩1,170,718 total
Apr 29 - Apr 30
includes taxes & fees
8.4/10 Very Good! (754 reviews)
Our family of four stayed for 3 nights in a two bedroom suite with ocean views. We booked it last minute for spring break. Overall, we had an amazing time and enjoyed our stay despite the cold temps. The room was clean. I saw no obvious signs of aging of furniture, fittings and walls - a huge plus ...
Reviewed on Apr 14, 2026
Montauk Manor
236 Edgemere St. Montauk NY
The price is ₩246,638 per night from Apr 24 to Apr 25
₩246,638
₩310,688 total
Apr 24 - Apr 25
includes taxes & fees
9.2/10 Wonderful! (1,324 reviews)
The kitchen was perfect, only thing missing was utensils. There is a local store on the way to the manor to pick some of those staples up from.
Reviewed on Apr 13, 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
The price is ₩350,983 per night from Apr 20 to Apr 21
₩350,983
₩429,076 total
Apr 20 - Apr 21
includes taxes & fees
8.8/10 Excellent! (1,007 reviews)
Front desk staff were amazing! The bar staff were very attentive and friendly. Rooms are clean, but definitely dated.
Reviewed on Apr 13, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Discover the most popular places to visit in Shelter Island
Havens House
You can spend an afternoon browsing the exhibits at Havens House during your trip to Shelter Island. Stroll along the area's beaches or simply enjoy its wineries.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
